title: Diastereoselective Michael reaction of chiral nickel(II) glycinate with nitroalkenes for asymmetric synthesis of β-substituted α,γ-diaminobutyric acid derivatives in water.
abstract: We have developed the first operationally simple and environmentally benign protocol for the aqueous asymmetric Michael addition reaction of chiral nickel(II) glycinate with nitroalkenes. The reactions proceeded smoothly in the presence of TBAB (tetrabutyl ammonium bromide) in neat water at room temperature and provided good yields of β-substituted α,γ-diaminobutyric acid derivatives with excellent diastereoselectivities.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zu chong zhi Road, Shanghai, 201203, People's Republic of China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.forename: Xun
authors.initials: X
authors.lastname: Ji
authors.forename: Jianmei
authors.initials: J
authors.lastname: Shi
authors.forename: Haifeng
authors.initials: H
authors.lastname: Sun
authors.forename: Hualiang
authors.initials: H
authors.lastname: Jiang
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
chemical_list: D000475:Alkenes; D009574:Nitro Compounds; D000644:Quaternary Ammonium Compounds; D014867:Water; D009532:Nickel; C009405:tetrabutylammonium; D005998:Glycine